32 - What the Teddy Bear Saw
Finch tries to hijack a surveillance videotape of him and Jack's nanny in a compromising position. When Maya has her wisdom teeth pulled, Nina attempts to convince Elliott not to help Maya get home from the dentist. Guest Star: Ana Gasteyer

33 - Steamed
Jack tricks Maya into getting the upstairs neighbor to move so he can build a steam room at work, while Nina frets about the arrival of her old modeling rival and friend.

34 - The Mask
A Halloween episode: Maya discovers how Jack deceived her on Halloween many years ago. Finch swears he's not afraid of the movie Psycho, as Elliott and he try to find out if Nina's friend Binnie really exists.

35 - Funny Girl
Finch challenges Maya to play a good practical joke. Jack looks into plastic surgery. Guest Star: Steve Carell

36 - Two Girls for Every Boy
After Finch conspires to set Maya up on a date with female model, Maya and she turn the tables on him. Meanwhile, after Jack insists that Nina and Elliott treat him just like anyone else at the office, their harsh sarcasm forces him to reconsider his decision.

37 - The Withholder
Elliott promises to get revenge after Finch is taken advantage of by a woman. Meanwhile, after making a bet with billionaire Donald Trump, Jack enlists Nina to help him lose weight.

38 - Puppetmaster
Maya is convinced that her new boyfriend is sending her messages by way of the puppets he uses on his children’s television show. Meanwhile, as Nina invests in an exclusive and trendy nightclub, Elliott regrets sharing his inner thoughts about being a woman with Jack and Finch. Guest Star: French Stewart

39 - The List
Jack turns to the staff for ideas to get back on the list of the most influential New Yorkers, while Star Wars's Mark Hamill stalks Finch. Guest Star: Mark Hamill

40 - How Nina Got Her Groove Back
Nina is despondent at the retirement of a longtime rival. Jack’s desire to gain fame by naming a park after himself backfires. Maya meets a man who constantly takes his shirt off in public. Elliott wears dangerous shoes. Guest Star: Christine Ebersole

41 - How the Finch Stole Christmas
Maya fights with Jack over the availability of a "Sneezing Charlie" doll. Finch seeks revenge for a measly Christmas gift. Nina criticizes a handsome man’s casual clothes. Guest Star: Listen for Kelsey Grammer as the narrator

42 - Slow Donnie
Maya tries to convince Elliott that his slow-witted brother is a fake. Meanwhile, Jack’s efforts to build a shelf for Finch uncovers a pneumatic tube message system hidden inside the office walls, and Nina accepts an influential designer’s gift of a parakeet. Guest Star: David Cross

43 - A Spy in the House of Me
Jack is upset when Maya’s old high school boyfriend suddenly reappears. Meanwhile, as Nina nervously prepares for a television talk show, Finch begins interviewing new internship candidates. Guest Star: Nancy O'Dell

44 - Lies & Dolls
Maya’s efforts to woo a handsome presidential candidate are disrupted when he falls for Nina instead. As Jack decides to give up his private office in order to work among the staff, Finch recognizes that a Six Million Dollar Man doll Elliott stole as a child is now a valuable collector’s item.

45 - Nina Sees Red (1)
Following his divorce, Finch’s dad starts dating Nina. Elliott scares Tyra Banks with Jack's stun gun. Guest Stars: Brian Dennehy, Tyra Banks

46 - Nina Sees Red (2)
Finch tries coming to grips with his dad’s engagement to Nina. As Jack prepares to bid on some solid gold golf tees once owned by Ernest Hemingway, Elliott asks him to speak with Tyra Banks and explain the stun gun incident. Guest Stars: Brian Dennehy, Tyra Banks

47 - Hostess to Murder
Maya’s plan for a murder mystery theme party backfires when a grouchy neighbor dies on her doorstep. Guest Star: Fred Willard

48 - Toy Story
When Maya gives him Elliott’s birthday present to wrap, Finch plays a practical joke by switching it with Persky’s gift. Meanwhile, a racehorse Jack co-owns with singer Robert Goulet begins acting up. Guest Star: Robert Goulet

49 - Miss Pretty
Finch tries to keep from being identified as the magazine’s new advice columnist. A mistake forces Nina to have lunch with an acquaintance she doesn’t really like. Elliott offends one of the magazine’s biggest advertisers.

50 - Maya's Nude Photos
Maya and Elliott clash with each other when her photography teacher asks her to do a nude self-portrait. Meanwhile, though Nina hires a new assistant, he spends all of his time entertaining Jack with magic and annoying Finch.

51 - And the Femmy Goes To...
Though happy to have been nominated for a Fashion Magazine Excellence Award, Maya is stunned to learn that it was for an article her father chose instead of the one she submitted. Elliott admits that the photo for which he was nominated was actually taken by a monkey. Nina struggles to come up with an acceptance speech. Finch schemes to get seated next to a model.

52 - Softball
Jack tries to replace Steve Garvey with Maya as pitcher for the office’s annual softball game against Cosmo. Guest Star: Steve Garvey

53 - Shaking Private Trainer
While Nina suggests Jack hire a personal trainer, Elliott feels left out when Maya and Finch collaborate on a screenplay.

54 - Nina's Choice
Maya challenges Nina to make better choices in life, especially when Nina has to choose between an escaped-convict ex-boyfriend and the FBI agent who’s looking for him. Meanwhile, Jack, Finch, and Elliott all start betting on each other’s habits and idiosyncrasies.

55 - The Odd Couple (1)
To impress an old high school classmate, Finch engineers a date with an emotionally vulnerable supermodel. In a separate effort to make an impression for a magazine article about art in the executive suite, Jack sends Elliott out to buy a suitable painting. But when he’s unhappy with Elliott’s choice, Jack buys one on his own, oblivious to its sexually charged subject matter. Guest Star: Rebecca Romijn

56 - The Odd Couple (2)
Finch struggles to get married to supermodel Adrienne before her ex-boyfriend finds out. Maya and Elliott argue whether or not Finch and Adrienne love each other. Guest Star: Rebecca Romijn